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Bridgeport, CT, USA to Chicago, IL, USA from $42: 10 ways by bus, train, flight or car

Compare Travel Options and Prices

from
Bridgeport, United States of America
to
Chicago, United States of America

How to Get from Bridgeport to Chicago: Cheapest, Fastest and Best Way

1Map provides directions to cities, towns, landmarks, attractions, and addresses worldwide, offering thousands of multi-modal routes to easily get you from point A to point B.

$42 by trainBest price
1361 kmDistance
6h 24m Fastest

Compare Train, Bus, Flight, and Driving Options

Get detailed, step-by-step directions below for your trip from Bridgeport to Chicago with 1Map travel planner. Easily compare ticket prices, explore various transport options, and find the best routes for a seamless and cost-effective travel experience.

Company
various
Train
Plane
Average Duration
6h  24m
Estimated price
$139-543
Recommended
Company
Amtrak
Train
Average Duration
21h  55m
Estimated price
$42-492
Cheapest
route map
Distance: 1361 km
Duration: 6h 24m

See more options

Company
various
Train
Plane
Average Duration
6h  51m
Estimated price
$54-253
Company
various
Train
Plane
Average Duration
6h  53m
Estimated price
$69-1390
Company
various
Train
Plane
Average Duration
6h  34m
Estimated price
$127-462
Company
various
Train
Bus
Plane
Average Duration
7h  25m
Estimated price
$1391-1392
Company
various
Train
Plane
Average Duration
7h  23m
Estimated price
$1393-1394
Company
various
Train
Plane
Train
Average Duration
9h  7m
Estimated price
$1395-1396
Company
Greyhound USA
Bus
Average Duration
24h  9m
Estimated price
$1397-1398
Company
various
Drive
Average Duration
14h  3m
Estimated price
$1399-5430
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Traveling From Bridgeport to Chicago

Your journey from Bridgeport, a charming waterfront town, to Chicago, a bustling metropolis rich in culture and architecture, offers a stark contrast between cozy small-town vibes and vibrant city life.

Best Neighborhoods in Chicago

Chicago boasts diverse neighborhoods, each with its own character and attractions.

Lincoln Park
• Home to the Lincoln Park Zoo, free to enter.
• Charming boutiques and restaurants along Armitage Avenue.
Wicker Park
• Known for its vibrant arts and music scene.
• Trendy cafes and vintage shops line the streets.
Magnificent Mile
• Famous for upscale shopping and dining options.
• Architectural landmarks showcase Chicago's rich history.

Best Times To Visit Chicago's Attractions

Timing your visits to Chicago's attractions can significantly enhance your experience.

Millennium Park
Visit early morning or late afternoon to enjoy more peaceful strolls.
The Art Institute of Chicago
Wednesdays and Thursdays are less crowded, perfect for art lovers.
Navy Pier
Visit on weekdays during the summer for fewer tourists and easier access.

Chicago Weather: What to Expect Year-Round

Chicago experiences a humid continental climate, with cold winters and warm summers that can affect your travel itinerary. The best times to visit are typically spring and fall, when the temperatures are mild, allowing you to fully enjoy the city's vibrant outdoor scenes.

Dining Recommendation

When in Chicago, try the deep-dish pizza at Pequod's, a restaurant famous for its crispy, caramelized crust and generous cheese layers—offering a delightful contrast to Bridgeport's more homestyle cuisine. This dining experience immerses you in a lively urban atmosphere, showcasing local ingredients and flavors that truly capture the essence of the city.

Bridgeport - Chicago operators

Explore transport companies operating between Bridgeport and Chicago, with prices starting at . These companies offer competitive pricing, flexible schedules, and comfortable travel experiences.

Train
Contact phone
877.690.5114
Website
https://new.mta.info/agency/metro-north-railroad

Train from Bridgeport to Grand Central Terminal

Average Duration
1h 42m
Estimated price
$540-545

Train from Bridgeport to Stamford

Average Duration
46m
Estimated price
$546-547
Contact phone
+1 800-872-7245
Website
https://www.amtrak.com/home.html

Train from Bridgeport Amtrak Station to New York Penn Station

Average Duration
1h 23m
Estimated price
$2531-4927

Train from Bridgeport Amtrak Station to Stamford Amtrak Station

Average Duration
27m
Estimated price
$2535-2536
Plane
Website
delta.com

Plane from New York La Guardia to Chicago Midway

Average Duration
2h 31m
Estimated price
$425-4921

Plane from New York La Guardia to Chicago O'Hare

Average Duration
2h 48m
Estimated price
$5435-5436
Website
southwest.com

Plane from Hartford to Chicago Midway

Average Duration
2h 31m
Estimated price
$4922-4923

Plane from New York La Guardia to Chicago Midway

Average Duration
2h 31m
Estimated price
$425-4921
Bus
Contact phone
+1 214-849-8100
Website
https://www.greyhound.com/

Bus from Bridgeport Bus Stop to Port Authority Bus Terminal

Average Duration
1h 55m
Estimated price
$1271-4926

Bus from Port Authority Bus Terminal to Indianapolis Bus Station

Average Duration
17h 10m
Estimated price
$5438-429
Website
palmlandlines.com

Bus from Indianapolis IN to Chicago IL

Average Duration
3h 20m
Estimated price
$1391-421

Frequently asked questions

Find out more about the route from Bridgeport to Chicago.

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The distance between Bridgeport and Chicago is approximately 752 miles or 845 miles by road. The typical travel times by various modes of transportation are 21 hours and 55 minutes by train, 6 hours and 15 minutes by train and flight, 14 hours and 3 minutes by car, and 19 hours and 8 minutes by bus. These travel times can vary depending on factors such as traffic, weather conditions, and transportation schedules.
The most cost-effective option for traveling from Bridgeport to Chicago is by bus, with prices ranging from $17 to $160. However, this option also takes the longest time, with a travel duration of 19 hours and 8 minutes. For those looking to save time and willing to spend a bit more, the fastest option is to take a train and then fly, which takes approximately 6 hours and 15 minutes and costs between $100 and $700.
The prices for a train ticket between Bridgeport and Chicago range from $42 to $492, depending on factors such as the type of train and class of seating. On the other hand, the prices for a bus ticket between Chicago and Bridgeport vary from $18 to $154, depending on the bus company and the level of service. It is advisable to compare prices and book tickets in advance to secure the best deals for your travel.
To travel from Bridgeport to Chicago without using public transportation, you can drive the distance of 845 miles. The journey typically takes around 14 hours and 3 minutes by car. Prices for renting a car to make this trip can range from $150 to $230, depending on the rental company and vehicle chosen.
The best way to travel from Bridgeport to Chicago without a car is by taking a bus. The bus journey takes approximately 19 hours and 8 minutes. Ticket prices can range from $17 to $160 depending on the bus company and the type of ticket you purchase. This option allows you to relax and enjoy the scenic views along the way while avoiding the hassle of driving.
Yes, there is a connection between Bridgeport and Chicago but there is no direct train or bus service. The train journey from Bridgeport to Chicago takes approximately 21 hours and 55 minutes with transfers at New York Penn Station. Alternatively, the bus journey takes approximately 19 hours and 8 minutes with transfers in Stamford and Ithaca, NY. Both options require multiple transfers and may have longer travel times compared to other modes of transportation.
The flight duration from New York La Guardia Airport to Chicago Midway Airport is approximately 2 hours and 15 minutes. This is the quickest and most efficient way to travel between the two cities. The cost of the flight may vary depending on the airline, booking time, and other factors, but on average, it can range from $150 to $300.
There are many accommodation options available in Chicago, with a variety of hotels to choose from. Prices for hotels in the area start at $58 per night, offering a range of budgets to suit different travelers. With over 1116 hotels to choose from, visitors to Chicago can find options that suit their preferences and needs.

Trips to Chicago